Podcast Summary:

Podcast: Hillsdale College K-12 Classical Education Podcast
Episode: Writing Letters of Recommendation and Advising Resume Creation
Date: November 3, 2025
Host: Scott Bertram
Guest: Jenny Pridgen, Director of Field Recruitment, Admissions Department, Hillsdale College

Episode Overview

This episode delves into the practicalities and best practices for writing letters of recommendation and crafting high school resumes, especially in the context of applying to Hillsdale College. Host Scott Bertram converses with Jenny Pridgen about what admissions officers look for in these application components, mistakes to avoid, and advice for teachers, counselors, students, and even parents. The episode offers insider insight into what makes a student stand out in a competitive admissions process at a classical educational institution.

Key Discussion Points & Insights

1. The Value and Purpose of Letters of Recommendation

• Do letters make a difference?
  • Jenny emphasizes their importance:

    "It can be really transformational to us in the application process. It gives some really good background on a student. It helps us either verify or contradict certain things that a student has said..." (02:07)

  • Letters bring "life" to an application that is otherwise "just paper."
• What Hillsdale looks for:
  • Letters should speak to:
    • Character
    • Work ethic
    • Academic abilities
  • Details and specific examples are most effective:

    "...given the background of, 'Oh, but we think this actually makes the student a really good fit for the college.' It can be so helpful." (03:02)

2. Best Practices and Pitfalls in Recommendation Letters

• Avoid:
  • Excessive autobiography:

    "...an excessive autobiography can really detract from the amount of space that you have to write about the student." (04:05)

  • Overusing templates or copying language for multiple students, as this lessens impact and authenticity.
• Recommended structure:
  • Begin with an anecdote:

    "I like to begin a letter with a brief...anecdote that really shows a student's character, work ethic, but also perhaps makes the reader want to continue reading..." (05:06, Scott Bertram)

  • Jenny affirms:

    "Oh, we love that. A little bit of color description. Those things are really great." (05:37)

3. Customization and Quantity of Letters

• Customizing for each college:
  • Helpful, but not essential unless a student is a particularly strong fit or the institution is a top choice. "Certainly not 10 variations" (06:22).
• How many letters to submit?:
  • Two academic letters, and optionally a third from someone like a coach or mentor.

  • "...three really sort of plumbs the depths of what we need to know. And at that point, we'd love for you to stop." (09:04)

• Who should write?:
  • Quality and insight matter more than a “big name.”

    "Only if that person really knows them well...if all they can say is, 'oh wow, I've met this person one time, they were great at bringing me coffee. That's not very helpful to us.'" (09:38)

  • If a recommender cannot genuinely write a positive letter, it is better to decline:

    "...if you feel like it would be a real struggle to have positive things to say...then I think having that opportunity and saying that you want what's best for them..." (07:20)

4. Differentiating Students

• When students from the same school compete:
  • Don’t feel pressured to rank or differentiate aggressively; focus on authentic, specific observations.

    "...as much as we really appreciate your desire to differentiate, you can leave that to us. You don't have to feel the responsibility..." (11:27)

  • Superlatives are only helpful if genuine.

5. Emphasis on Work Ethic and Character

• Academics are visible on the transcript; the letter should illuminate what’s “behind all that”—work ethic and character (10:12).
• Third-party recommendations (like coaches) can focus on these attributes, especially if unable to comment directly on academics (08:17).

6. High School Resumes: Role & Expectations

• Why require a resume now?
  • Hillsdale now requires a resume to better understand student involvement and “what makes the student them outside the classroom.” (12:49)
• What to include:
  • More than just job experience—service, clubs, organizations, church, community involvement, or family responsibilities.

    "...it doesn't have to be an official thing for you to include it on your resume. If it's just something that you spend a lot of your time doing, we'd love to hear about it." (14:08)

  • Activities should cover grades 9-12 and list estimated time commitments.
• Breadth vs. Depth:
  • It’s not about “collecting” activities for appearance:

    "Don’t do something just for the resume. Do it because you love it. And usually we can tell that it’s important to you." (14:08)

  • Both specialists and generalists are welcomed in the admissions pool.
• Noting future intentions:
  • It’s helpful but not essential to indicate which activities a student hopes to continue in college (15:27).

Notable Quotes & Memorable Moments

• On Authenticity:

  "We’ve gotten letters regarding different students from the same person before, and they've used almost the exact same words...it made it a lot less impactful." – Jenny Pridgen (04:05)

• On Letters from Well-Known Individuals:

  "Should I have them write a letter? And the answer is always, only if they know you well." – Jenny Pridgen (09:38)

• On What Matters Most:

  "If we had to choose, it would be some combination of work ethic or character, probably actually less academics..." – Jenny Pridgen (10:12)

• On the Role of the Resume:

  "...what makes the student them outside the classroom." – Jenny Pridgen (12:49)

• On Breadth vs. Depth:

  "Some students will do a lot in one area...and they'll say, oh, is that better? Or should I get involved in, you know, 17 routine things...We like lots of different students at Hillsdale." – Jenny Pridgen (14:08)

Important Segment Timestamps

• [02:07] – Significance of letters of recommendation
• [03:02] – What qualities make a strong letter
• [04:05] – Pitfalls to avoid in writing
• [05:37] – The value of anecdotes in letters
• [06:22] – Customizing letters for specific colleges
• [07:20] – When to decline writing a letter
• [09:04] – Ideal number of recommendation letters
• [09:38] – Value of a well-known letter writer
• [10:12] – What matters most in letters
• [12:49] – Why resumes are now required
• [14:08] – What to include on the activity resume
• [15:27] – Indicating future activity intentions

Closing Thoughts

This episode offers a practical roadmap for anyone involved in the college admissions process—teachers, counselors, students, and parents alike. The key takeaway is the importance of authentic, specific, and heartfelt communication, both in letters of recommendation and personal resumes. Hillsdale’s approach is holistic and values insight into who the student is beyond grades and scores, making narrative, character, and real interests matter most.